IL31550A - Thionine derivatives and preparation thereof - Google Patents
Thionine derivatives and preparation thereofInfo
- Publication number
- IL31550A IL31550A IL31550A IL3155069A IL31550A IL 31550 A IL31550 A IL 31550A IL 31550 A IL31550 A IL 31550A IL 3155069 A IL3155069 A IL 3155069A IL 31550 A IL31550 A IL 31550A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- halogen
- represents hydroxy
- residue
- compound
- Prior art date
Links
- 150000000552 thionines Chemical class 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 16
- 229910052736 halogen Chemical group 0.000 claims description 15
- 150000002367 halogens Chemical group 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 9
- 239000011707 mineral Substances 0.000 claims description 9
- 235000010755 mineral Nutrition 0.000 claims description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 3
- 150000004986 phenylenediamines Chemical class 0.000 claims 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 2
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 claims 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims 2
- 241000282320 Panthera leo Species 0.000 claims 1
- 125000003963 dichloro group Chemical group Cl* 0.000 claims 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 claims 1
- 125000001145 hydrido group Chemical group *[H] 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims 1
- 239000011592 zinc chloride Substances 0.000 claims 1
- 235000005074 zinc chloride Nutrition 0.000 claims 1
- 239000000243 solution Substances 0.000 description 18
- 206010028980 Neoplasm Diseases 0.000 description 14
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
- 239000002156 adsorbate Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- 230000000875 corresponding effect Effects 0.000 description 7
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000000824 cytostatic agent Substances 0.000 description 6
- 230000001085 cytostatic effect Effects 0.000 description 6
- 229920000669 heparin Polymers 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- -1 methylene toluidine Chemical class 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 4
- 229950000688 phenothiazine Drugs 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 4
- 206010003445 Ascites Diseases 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Chemical group 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 210000000952 spleen Anatomy 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- HZOPTYGSWRGRBS-UHFFFAOYSA-N 2-(2-hydroxyethylamino)ethanol;hydrobromide Chemical compound Br.OCCNCCO HZOPTYGSWRGRBS-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229910000906 Bronze Inorganic materials 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000010974 bronze Substances 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KUUVQVSHGLHAKZ-UHFFFAOYSA-N thionine Chemical compound C=1C=CC=CSC=CC=1 KUUVQVSHGLHAKZ-UHFFFAOYSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- XJCXPCWYMDOODD-UHFFFAOYSA-N Br.C=1C=CC=CSC=CC=1 Chemical compound Br.C=1C=CC=CSC=CC=1 XJCXPCWYMDOODD-UHFFFAOYSA-N 0.000 description 1
- FHOODEIONORORX-UHFFFAOYSA-N Cl.Cl.Cl.Br.Br Chemical compound Cl.Cl.Cl.Br.Br FHOODEIONORORX-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 102000007327 Protamines Human genes 0.000 description 1
- 108010007568 Protamines Proteins 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- DCEMJHTZJLNIIA-UHFFFAOYSA-L [Cr](=O)(=O)(O)O.OO Chemical compound [Cr](=O)(=O)(O)O.OO DCEMJHTZJLNIIA-UHFFFAOYSA-L 0.000 description 1
- LIABKAQKQSUQJX-UHFFFAOYSA-N [Mn].[Pb] Chemical compound [Mn].[Pb] LIABKAQKQSUQJX-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 230000001399 anti-metabolic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 231100000026 common toxicity Toxicity 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- SFQOCJXNHZJOJN-UHFFFAOYSA-H dialuminum;dioxido-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=S.[O-]S([O-])(=O)=S.[O-]S([O-])(=O)=S SFQOCJXNHZJOJN-UHFFFAOYSA-H 0.000 description 1
- 229940075933 dithionate Drugs 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 230000011278 mitosis Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 229940048914 protamine Drugs 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 229950003937 tolonium Drugs 0.000 description 1
- HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUEE001491 | 1968-02-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL31550A0 IL31550A0 (en) | 1969-04-30 |
| IL31550A true IL31550A (en) | 1972-06-28 |
Family
ID=10995247
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL31550A IL31550A (en) | 1968-02-16 | 1969-02-04 | Thionine derivatives and preparation thereof |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3641016A (en)) |
| AT (1) | AT287732B (en)) |
| BE (1) | BE728439A (en)) |
| BR (1) | BR6906449D0 (en)) |
| CH (1) | CH520160A (en)) |
| CS (1) | CS157051B2 (en)) |
| DE (1) | DE1906527C3 (en)) |
| DK (1) | DK131628C (en)) |
| FI (1) | FI50419C (en)) |
| FR (1) | FR2002028A1 (en)) |
| GB (1) | GB1256733A (en)) |
| IL (1) | IL31550A (en)) |
| NL (1) | NL6902424A (en)) |
| PL (1) | PL72594B1 (en)) |
| SE (1) | SE361480B (en)) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1408734A (en) * | 1972-11-06 | 1975-10-01 | Misubishi Chemical Ind Ltd | Basic dyestuff mixtures |
| GB0113121D0 (en) * | 2001-05-30 | 2001-07-18 | Univ Leeds | Biologically active photosensitisers |
| US20080193873A1 (en) * | 2002-06-17 | 2008-08-14 | Verification Technologies, Inc. | Changing light absorption by disruption of conjugation |
| US7368221B2 (en) * | 2002-06-17 | 2008-05-06 | Verification Technologies, Inc. | Changing light absorption by disruption of conjugation |
| WO2005054217A1 (en) * | 2003-11-28 | 2005-06-16 | Photopharmica Limited | Developments in biologically active methylene blue derivatives (2) |
| AU2005286235C1 (en) * | 2004-09-23 | 2013-08-22 | TauRx Therapeutics Management Ltd | Methods of chemical synthesis and purification of diaminophenothiazinium compounds including Methylthioninium Chloride (MTC) |
| US7220879B2 (en) | 2004-10-01 | 2007-05-22 | Rohm And Haas Company | Method for inhibiting polymerization of (meth)acrylic acid and its esters using an inhibitor and a process for making a compound useful as such an inhibitor |
| US7101997B2 (en) * | 2004-10-07 | 2006-09-05 | Honeywell International Inc. | Method for producing phenothiazinium compounds |
| HRP20100614T4 (hr) * | 2006-03-29 | 2019-08-09 | Wista Laboratories Ltd. | Soli 3,7-diamino-10h-fenotiazina i njihova uporaba |
| MY162313A (en) | 2006-07-11 | 2017-05-31 | Wista Lab Ltd | Methods of synthesis and/or purification of diaminophenothiazinium compounds |
| US9795242B2 (en) | 2013-02-14 | 2017-10-24 | Cirkul, Inc. | Additive delivery systems and containers |
| US10888826B2 (en) | 2014-11-21 | 2021-01-12 | Cirkul, Inc. | Adjustable additive cartridge systems and methods |
| AU2015349694B2 (en) | 2014-11-21 | 2020-05-14 | Cirkul, Inc. | Adjustable additive cartridge systems |
| EP3375777A1 (en) | 2017-03-15 | 2018-09-19 | MIKROCHEM spol. s.r.o. | Method for preparation of 3,7-bis-(dimethylamino)-phenothiazin-5-ium chloride or bromide |
| CN116178987B (zh) * | 2023-03-02 | 2024-06-28 | 山东中康国创先进印染技术研究院有限公司 | 一种可用于对纺织品进行染色的蓝色系染料及其染色方法 |
-
1969
- 1969-02-03 US US796216A patent/US3641016A/en not_active Expired - Lifetime
- 1969-02-04 IL IL31550A patent/IL31550A/en unknown
- 1969-02-05 GB GB1256733D patent/GB1256733A/en not_active Expired
- 1969-02-10 DE DE1906527A patent/DE1906527C3/de not_active Expired
- 1969-02-11 AT AT135169A patent/AT287732B/de not_active IP Right Cessation
- 1969-02-14 BE BE728439D patent/BE728439A/xx unknown
- 1969-02-14 CH CH229569A patent/CH520160A/de not_active IP Right Cessation
- 1969-02-14 FI FI690477A patent/FI50419C/fi active
- 1969-02-14 BR BR206449/69A patent/BR6906449D0/pt unknown
- 1969-02-14 FR FR6903561A patent/FR2002028A1/fr not_active Withdrawn
- 1969-02-14 SE SE02078/69A patent/SE361480B/xx unknown
- 1969-02-14 DK DK80669*#A patent/DK131628C/da active
- 1969-02-14 NL NL6902424A patent/NL6902424A/xx unknown
- 1969-02-15 PL PL1969131750A patent/PL72594B1/pl unknown
- 1969-02-17 CS CS105969A patent/CS157051B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI50419C (fi) | 1976-03-10 |
| SE361480B (en)) | 1973-11-05 |
| FR2002028A1 (en)) | 1969-10-03 |
| GB1256733A (en)) | 1971-12-15 |
| PL72594B1 (en)) | 1974-08-30 |
| CS157051B2 (en)) | 1974-08-23 |
| BE728439A (en)) | 1969-07-16 |
| DK131628B (da) | 1975-08-11 |
| FI50419B (en)) | 1975-12-01 |
| BR6906449D0 (pt) | 1973-01-16 |
| IL31550A0 (en) | 1969-04-30 |
| US3641016A (en) | 1972-02-08 |
| CH520160A (de) | 1972-03-15 |
| DE1906527C3 (de) | 1981-07-02 |
| NL6902424A (en)) | 1969-08-19 |
| DK131628C (da) | 1976-02-16 |
| AT287732B (de) | 1971-02-10 |
| DE1906527B2 (de) | 1980-11-06 |
| DE1906527A1 (de) | 1969-12-04 |
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